Field of the Invention
The present invention relates to quinolines of the formula I ##STR2## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3, R.sup.4 in each case independently of one another are hydrogen, hydroxyl, nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkoxyalkyl,
R.sup.5, R.sup.6 in each case independently of one another are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio; PA1 R.sup.7 is hydrogen, C.sub.1 -C.sub.4 -alkyl, formyl, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl; PA1 R.sup.8 is hydrogen, formyl, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl or C.sub.1 -C.sub.8 -alkylcarbonyl, it being possible for these groups to be partially or fully halogenated, C.sub.3 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.7 -cycloalkenyl, it being possible for these radicals to be partially or fully halogenated, PA1 aryl or hetaryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy; PA1 R.sup.7 and R.sup.8 together form a bond; PA1 R.sup.9 is aryl or hetaryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substituents, in turn, can have attached to them one to three of the following substituents: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy; PA1 halogen: fluorine, chlorine, bromine and iodine; PA1 alkyl: straight-chain or branched alkyl groups having 1 to 8 carbon atoms, eg. C.sub.1 -C.sub.6 -alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; PA1 haloalkyl, or partially or fully halogenated alkyl: straight-chain or branched alkyl groups having 1 to 4 or 8 carbon atoms (as mentioned above), it being possible for the hydrogen atoms in these groups to be partially or fully replaced by halogen atoms (as mentioned above), eg. C.sub.1 -C.sub.2 -haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl; PA1 alkoxy: straight-chain or branched alkoxy groups having 1 to 4 carbon atoms, eg. C.sub.1 -C.sub.3 -alkoxy, such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy; PA1 alkoxyalkyl: straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above) which have attached to them in any position a straight-chain or branched alkoxy group (as mentioned above) having, in the case of C.sub.1 -C.sub.4 -alkoxyalkyl, 1 to 4 carbon atoms, such as methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 2-n-propoxyethyl and 2-butoxyethyl; PA1 haloalkoxy: straight-chain or branched alkoxy groups having 1 to 4 carbon atoms (as mentioned above), it being possible for the hydrogen atoms in these groups to be partially or fully replaced by halogen atoms (as mentioned above), eg. C.sub.1 -C.sub.2 -haloalkoxy, such as chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy and pentafluoroethyloxy; PA1 alkylthio: straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (--S--), eg. C.sub.1 -C.sub.4 -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, n-butylthio and tert-butylthio; PA1 alkoxycarbonyl: straight-chain or branched alkoxy groups having 1 to 4 C atoms (as mentioned above) which are bonded to the skeleton via a carbonyl group (--CO--); PA1 alkenyl: straight-chain or branched alkenyl groups having 2 to 8 carbon atoms and a double bond in any position, eg. C.sub.2 -C.sub.6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; PA1 alkynyl: straight-chain or branched alkynyl groups having 2 to 8 carbon atoms and a triple bond in any position, eg. C.sub.2 -C.sub.6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; PA1 cycloalkyl: monocyclic alkyl groups having 3 to 7 carbon ring members, eg. C.sub.3 -C.sub.7 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; PA1 cycloalkenyl: monocyclic alkyl groups having 5 to 7 carbon ring members which contain one or more double bonds, eg. C.sub.5 -C.sub.7 -cycloalkenyl, such as cyclopentenyl, cyclohexenyl and cycloheptenyl; PA1 non-aromatic 4- to 8-membered rings which, besides carbon, additionally contain one or two oxygen, sulfur or nitrogen atoms as ring members, such as saturated 5- or 6-membered rings having 1 or 2 nitrogen and/or oxygen atoms, such as 3-tetrahydrofuranyl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-morpholinyl and 3-morpholinyl; PA1 aryl: monocyclic or polycyclic aromatic groups having 6 to 10 C atoms, such as phenyl and naphthyl; PA1 arylalkyl: aryl groups (as mentioned above) which, in the case of aryl(C.sub.1 -C.sub.4)alkyl, are bonded to the skeleton via alkyl groups having 1 to 4 carbon atoms (as mentioned above), eg. phenyl(C.sub.1 -C.sub.4)alkyl, such as benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1-phenylethyl, 1-phenylpropyl and 1-phenylbutyl; PA1 aryloxy: aryl groups (as mentioned above) which are bonded to the skeleton via an oxygen atom (--O--), such as phenoxy, 1-naphthoxy and 2-naphthoxy; PA1 hetaryl: aromatic mono- or polycyclic radicals which, besides carbon ring members, can additionally contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, eg.: PA1 5-membered hetaryl bonded via nitrogen and containing 1 to 4 nitrogen atoms, or benzo-fused 5-membered hetaryl bonded via nitrogen and containing 1 to 3 nitrogen atoms: 5-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms, respectively, as ring members and in which 2 adjacent carbon ring members or one nitrogen and one adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one of the nitrogen ring members; PA1 6-membered hetaryl containing 1 to 3, or 1 to 4, respectively, nitrogen atoms: 6-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 3, or 1 to 4, respectively, nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; PA1 benzo-fused 6-membered hetaryl containing 1 to 4 nitrogen atoms: 6-membered hetaryl ring groups in which 2 adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline. PA1 dialkylamino: an amino group which has attached to it two straight-chain or branched alkyl groups which are independent of one another and have attached to them in each case 1 to 6 carbon atoms as mentioned above; PA1 alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms which are bonded to the skeleton via a carbonyl group (--CO--); PA1 alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms which are bonded to the skeleton via a sulfonyl group (--SO.sub.2 --); PA1 alkylsulfoxyl: straight-chain or branched alkyl groups having 1 bis 6 carbon atoms which are bonded to the skeleton via a sulfoxyl group (--S(.dbd.O)--); PA1 alkylsulfonyloxy: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms which are bonded to the skeleton via a sulfonyloxy group (--SO.sub.2 --O); PA1 alkylcarbonyloxy: straight-chain or branched alkyl groups having 1 to 10 carbon atoms which are bonded to the skeleton via a carbonyloxy group (--CO--O); PA1 alkoxycarbonyl: straight-chain or branched alkyl groups having 1 bis 6 carbon atoms which are bonded to the skeleton via a oxycarbonyl group (--OC(.dbd.O)--). PA1 R.sup.1, R.sup.2, R.sup.3, R.sup.4 in each case independently of one another are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkoxyalkyl, PA1 R.sup.5 and R.sup.6 in each case independently of one another are hydrogen, C.sub.1 -C.sub.2 -alkyl or halogen PA1 two of the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 are hydrogen; PA1 three of the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 are hydrogen; PA1 R.sup.3 =cyano, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyloxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -haloalkoxy; preferably halogen, C.sub.1 -C.sub.3 -alkyl, in particular chlorine and methyl; PA1 R.sup.5 and R.sup.6 are hydrogen, halogen, methyl, especially hydrogen; PA1 R.sup.5 is hydrogen, methyl, chlorine, especially hydrogen; PA1 R.sup.6 is hydrogen; PA1 R.sup.7 is hydrogen, methyl, formyl, C.sub.1 -C.sub.2 -alkylcarbonyl, especially hydrogen; PA1 R.sup.7 and R.sup.8 are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.4 -C.sub.6 -cycloalkyl, formyl, C.sub.1 -C.sub.2 -alkylcarbonyl; PA1 R.sup.8 is hydrogen, formyl, C.sub.1 -C.sub.2 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkyl, C.sub.4 -C.sub.6 -cycloalkyl; especially preferably hydrogen, formyl, CH.sub.3 CO, C.sub.1 -C.sub.4 -alkyl; furthermore preferably hydrogen, C.sub.1 -C.sub.4 -alkyl, especially preferably hydrogen, methyl, ethyl, i-propyl, n-butyl, especially hydrogen; PA1 R.sup.7 and R.sup.8 especially preferably form a joint bond; PA1 R.sup.9 is aryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substituents, in turn, can have attached to them one to three of the following substituents: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy; PA1 preferably aryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, phenyl, phenyloxy. PA1 the compounds 1.1a-1.192a, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is CH.sub.3. PA1 the compounds 1.1b-1.192b, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is C.sub.2 H.sub.5. PA1 the compounds 1.1c-1.192c, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is i--C.sub.3 H.sub.7. PA1 the compounds 1.1d-1.192d, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is c--C.sub.5 H.sub.9. PA1 the compounds 1.1e-1.192e, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is CH.sub.2 --C.sub.6 H.sub.5. PA1 the compounds 1.1f-1.192f, which differ from the corresponding compounds 1.1-1.192 of Table 1 by the fact that the substituent R.sup.8 is COCH.sub.3. PA1 I. a solution of 90 parts by weight of a compound I according to the invention and 10 parts by weight of N-methyl-2-pyrrolidone, which is suitable for use in the form of microdrops; PA1 II. a mixture of 10 parts by weight of a compound I according to the invention, 70 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate, 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil; a dispersion is obtained by finely distributing the solution in water; PA1 III. an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 40 parts by weight of cyclohexanone, 30 parts by weight of iso-butanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil; PA1 IV. an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 25 parts by weight of cyclohexanone, 55 parts by weight of a mineral oil fraction of boiling point 210 to 280.degree. C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil; PA1 V. a mixture, ground in a hammer mill, of 80 parts by weight of a preferably solid compound I according to the invention, 3 parts by weight of sodium di-iso-butylnaphthalene-.alpha.-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel; a spray mixture is obtained by finely distributing the mixture in water; PA1 VI. an intimate mixture of 3 parts by weight of a compound I according to the invention and 97 parts by weight of finely divided kaolin; this dust comprises 3% by weight of active ingredient; PA1 VII. an intimate mixture of 30 parts by weight of a compound I according to the invention, 62 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation imparts good adherence properties to the active ingredient; PA1 VIII. a stable aqueous dispersion of 40 parts by weight of a compound I according to the invention, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, and this dispersion can be diluted further; PA1 IX. a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 50 parts by weight of a paraffinic mineral oil. PA1 sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis(thiocarbamoyl) disulfide; PA1 nitro derivatives such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl 5-nitro-isophthalate; PA1 heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-bis(dimethylamino)-phosphinyl!-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo4,5-b!quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))benzimidazole, 2-(thiazolyl-(4))benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, PA1 N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thione 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxylic cyclohexylamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, PA1 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N-3-(p-tert-butylphenyl)-2-methylpropyl!-cis-2,6-dimethylmorpholine, N-3-(p-tert-butylphenyl)-2-methylpropyl!piperidine, 1-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl!-1H-1,2,4-triazo le, 1-2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl!-1H-1,2,4-tri azole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, (2-chlorophenyl)-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, 2-(4-chlorophenyl)ethyl!-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol, 1-3-(2-chlorophenyl)-1-(4-fluorophenyl)oxiran-2-ylmethyl!-1H-1,2,4-triazo le and PA1 a variety of fungicides such as dodecylguanidine acetate, 3-3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl!glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-furoyl(2)-DL-alaninate, methyl N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-DL-alaninate, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alaninate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione , 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-N-(ethylaminocarbonyl)-2-methoximino!-acetamide, 1-2-(2,4-dichlorophenyl)pentyl!-1H-1,2,4-triazole, 2,4-difluoro-.alpha.-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chlor o-2-aminopyridine, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole, PA1 strobilurins such as methyl E-methoximino-.alpha.-(o-tolyloxy)-o-tolyl!acetate, methyl E-2-{2-6-(2-cyanophenoxy)pyridimin-4-yloxy!phenyl}-3-methoxyacrylate, N-methyl-E-methoximino-.alpha.-(2,5-dimethyloxy)-o-tolyl!acetamide. PA1 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile. PA1 N-morpholinyl-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-acrylamide.
and to the N-oxides and the acid addition salts of the quinolines of the formula I, with the exception of the compounds where the radicals are defined as follows:
______________________________________ 1 a-d R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = C.sub.6 H.sub.5, 4-Cl--C.sub.6 H.sub.4, 2,4-di-Cl--C.sub.6 H.sub.3, 2,4-di-Br--C.sub.6 H.sub.3, 1 e-h R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = 4-Cl--C.sub.6 H.sub.4, 2,4-di-Cl--C.sub.6 H.sub.3, in each case in the form of the N-oxide and the HCl salt, 1 i R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = 4-Br--C.sub.6 H.sub.4 HBr salt 1 j-k R.sup.1,2,3,4,6,8 = H; R.sup.5 = CH.sub.3 ; R.sup.7 = H, CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5 1 m R.sup.1,3,4,6,7,8 = H; R.sup.2,5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 1 n R.sup.1 = O--CH.sub.3 ; R.sup.2,3,4,6,7,8 = H; R.sup.5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5 HCl salt, 1 o-q R.sup.1,3,4,5,6,7,8 = H; R.sup.2 = CH.sub.3 ; R.sup.9 = 4-NO.sub.2 --C.sub.6 H.sub.4 ; HCl salt, N-oxide 1 r-s R.sup.1,2,4,5,6,7,8 = H; R.sup.3 = Cl; R.sup.9 = 4-NO.sub.2 --C.sub.6 H.sub.4, 4-Cl--C.sub.6 H.sub.4 1 t-u R.sup.1,2,3,4,6,7,8 = H; R.sup.5 = Cl; R.sup.9 = 4-Cl--C.sub.6 H.sub.4, 2,4-di-Cl--C.sub.6 H.sub.3 1 v-x R.sup.1,4,6,7 = H; R.sup.3 = H,; R.sup.2 = H,CH.sub.3 O; R.sup.5 = CH.sub.3 R.sup.8,9 = CH.sub.2 CH.sub.2 Cl HCl salt, 1 x R.sup.1,4,6,7 = H; R.sup.3 = Cl R.sup.2 = H; R.sup.5 = CH.sub.3 R.sup.8,9 = CH.sub.2 CH.sub.2 Cl HCl salt, 1 y R.sup.1,4,6,7 = H; R.sup.3 = H; R.sup.2 = Cl; R.sup.5 = H R.sup.8,9 = CH.sub.2 CH.sub.2 Cl HCl salt, 1 z R.sup.1,2,4,5,6,7,8 = H; R.sup.3 = Cl; R.sup.9 = CH.sub.2 -3-Py, 2 a-b R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = quinolin-4-yl, di-N-oxide, 2 c R.sup.1,2,3,4,6,7,8 = H; R.sup.5 = CH.sub.3 ; R.sup.9 = quinolin-4-yl, di-N-oxide, 2 d-o R.sup.1,2,3,4,5,6 = H; R.sup.9 = C.sub.6 H.sub.5, C.sub.6 H.sub.5 N-oxide, 4-Cl--C.sub.6 H.sub.4, 4-Cl--C.sub.6 H.sub.4 N-oxide, 4-Br--C.sub.6 H.sub.4, 4-Br--C.sub.6 H.sub.4 N-oxide, 2,4-Cl--C.sub.6 H.sub.3, 2,4-Cl--C.sub.6 H.sub.3 N-oxide, 2,4-Br--C.sub.6 H.sub.3, 2,4-Br--C.sub.6 H.sub.3 N-oxide, 4-(CH.sub.3).sub.2 N--C.sub.6 H.sub.4, 4-(CH.sub.3).sub.2 N--C.sub.6 H.sub.4 N-oxide, 2 p-q R.sup.1,3,6 = H; R.sup.5 = CH.sub.3, R.sup.9 = C.sub.6 H.sub.5 ; R.sup.2 = OCH.sub.3, R.sup.4 = OCH.sub.3 ; 2 r-s R.sup.1,3,6 = H; R.sup.5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5 ; R.sup.2 = OCH.sub.2 CH.sub.3 ; R.sup.4 = OCH.sub.2 CH.sub.3 ; 2 t-v R.sup.1,2,3,4,6 = H; R.sup.5 = Cl; R.sup.9 = C.sub.6 H.sub.5, 4-Cl--C.sub.6 H.sub.4, 2,4-Cl--C.sub.6 H.sub.3, 2 w R.sup.1,2,4,5,6 = H; R.sup.3 = Cl; R.sup.9 = C.sub.6 H.sub.5, 2 x R.sup.1,2,3,4,6 = H; R.sup.5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 2 y R.sup.1,2,3,4 = H; R.sup.5,6 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 2 z R.sup.2,3,4,6 = H; R.sup.1,5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 3 a R.sup.1,3,4,6 = H; R.sup.2,5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 3 b R.sup.1,2,3,6 = H; R.sup.4,5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 3 c R.sup.2,4,6 = H; R.sup.1,3,5 = CH.sub.3 ; R.sup.9 = C.sub.6 H.sub.5, 3 d R.sup.1,3,6 = H; R.sup.2,4,5 = CH.sub.3 ; R.sup.9 = C.sub.6 ______________________________________ H.sub.5,
to a process for their preparation, to fungicidal compositions, and to their use for controlling harmful fungi.